300-38-9

Basic information

• Product Name: 3,5-Dibromo-L-tyrosine
• Synonyms: H-PHE(3,5-BR2, 4-OH)-OH DIHYDRATE;H-TYR(3,5-BR 2)-OH 2H2O;L-(3,5-DIBROMO, 4-HYDROXY)PHENYLALANINE DIHYDRATE;L-(3,5-DIBROMO)TYROSINE DIHYDRATE;L-Tyr(3',5'-Br2);5,5'-Dibromo-2,2'-dihydroxybenzil;Dibromotyrosine;3,5-Dibromo-L-tyrosine
• CAS NO: 300-38-9
• Molecular Formula: C₉H₉Br₂NO₃
• Molecular Weight: 338.98
• EINECS: 206-091-5
• Product Categories: Pharmaceutical Raw Materials
• Mol File: 300-38-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 245°C
• Boiling Point: 416.6°Cat760mmHg
• Flash Point: 205.7°C
• Appearance: /
• Density: 1.9706 (rough estimate)
• Vapor Pressure: 1.1E-07mmHg at 25°C
• Refractive Index: 0.8 ° (C=5, 1mol/L HCl)
• Storage Temp.: Store at RT.
• Solubility: Aqueous Base (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
• PKA: 2.17, 6.45, 7.60(at 25℃)
• Merck: 14,3030
• CAS DataBase Reference: 3,5-Dibromo-L-tyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dibromo-L-tyrosine(300-38-9)
• EPA Substance Registry System: 3,5-Dibromo-L-tyrosine(300-38-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 300-38-9(Hazardous Substances Data)

Usage

Description

3,5-Dibromo-L-tyrosine is a bromoamino acid derivative of L-tyrosine, which is one of the 22 proteinogenic amino acids utilized by cells to synthesize proteins. 3,5-Dibromo-L-tyrosine features bromo-substituents at positions C-3 and C-5 of the benzyl group, and it is characterized by its crystalline chemical properties.

Uses

Used in Pharmaceutical Industry:
3,5-Dibromo-L-tyrosine is used as a building block for the synthesis of various pharmaceutical compounds, particularly those with potential applications in the treatment of diseases. Its unique structure allows for the development of novel drugs with specific targeting and therapeutic properties.
Used in Research and Development:
In the field of research and development, 3,5-Dibromo-L-tyrosine serves as an important compound for studying the effects of halogenation on the properties and functions of amino acids. It can be used to investigate the role of bromine substitution in protein structure, stability, and function, as well as to explore its potential applications in drug design and development.
Used in Chemical Synthesis:
3,5-Dibromo-L-tyrosine is utilized as a key intermediate in the chemical synthesis of various organic compounds, including those with potential applications in the fields of materials science, pharmaceuticals, and agrochemicals. Its unique structural features make it a valuable starting material for the development of new molecules with specific properties and functions.

InChI:InChI=1/C9H9Br2NO3/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,7,13H,3,12H2,(H,14,15)/t7-/m0/s1

Upstream product

• 60-18-4 L-tyrosine 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 355857-30-6 (+)-(S)-methyl 3-(3,5-dibromo-4-hydroxyphenyl)-2-(2-methylprop-2-yloxycarbamoyl)propanoate 
• 67470-21-7 3',5'-dibromo-L-tyrosine methyl ester 
• 3417-91-2 L-tyrosine methyl ester HCl 

Downstream Products

• 91384-03-1 3,5-dibromo-L-tyrosine ethyl ester 
• 537-24-6 3,5-dibromo-DL-tyrosine 
• 67470-21-7 3',5'-dibromo-L-tyrosine methyl ester 
• 111820-85-0 (2S)-2-benzyloxycarbonylamino-3-(3,5-dibromo-4-hydroxyphenyl)propionic acid 
• 6893-00-1 3,5,3',5'-tetrabromo-L-thyronine 
• 57203-13-1 (S)-3-(3,5-Dibromo-4-hydroxy-phenyl)-2-(3-ethylcarbamoylsulfanyl-propionylamino)-propionic acid 
• 17194-82-0 2-(4-hydroxyphenyl)acetamide 
• 134755-34-3 3,5-dibromo-4-hydroxy-β-phenethylamine 
• 556-02-5 ?Tyr 
• 58960-71-7 N-[(1,1-dimethylethoxy)carbonyl]-3,5-dibromo-L-tyrosine 
• 943036-59-7 C₂₅H₂₈Br₂N₂O₇ 
• 943036-60-0 C₃₃H₃₃Br₂I₂N₃O₉ 
• 768360-59-4 (3,5-dibromo-Tyr)-Ser-Leu-OH 
• 768360-55-0 Boc-(3,5-dibromo-Tyr)-Ser-Leu-OMe 

Relevant articles and documents

Preparation of 3-bromo-l-tyrosine and 3,5-dibromo-l-tyrosine

l-Tyrosine is converted to 3-bromo-l-tyrosine in good yield by reaction with 1.2 equiv. of DMSO in HBr/AcOH, while reaction with 2.2 equiv. of DMSO under comparable conditions results in formation of 3,5-dibromo-l-tyrosine in good yield. This is the simplest, safest and most efficient method for the preparation of gram quantities of either 3-bromo-l-tyrosine or 3,5-dibromo-l-tyrosine.

Convenient access to L-3,4,5-trioxygenated phenylalanine compounds from L-tyrosine

A convenient and efficient synthesis of L-3,4,5-trioxygenated phenylalanine derivatives from L-tyrosine was developed. Dibromo phenylalanine is converted easily to bis-phenol via copper-catalyzed hydroxylation. The synthetic potential of this methodology has been demonstrated by efficient synthesis of L-3,4,5-trimethoxyphenylalanine methyl ester and one key intermediate of Trabectedin.

Synthesis and trypanocide activity of chloro-l-tyrosine and bromo-l-tyrosine derivatives

Twenty-two halogenated l-tyrosine derivatives were synthesized to examine new substances for the treatment of Chagas disease. The synthesis of these derivatives with different degree of substitution in the amino group with methyl iodide, giving primary, tertiary, and quaternary amino acids. All compounds were tested in vitro against intracellular amastigotes of Trypanosoma cruzi, and the cytotoxicity were evaluated over monocytic cell line U-937. Compound 25 was the most active against T. cruzi with a EC50 of 75.52 μM compared with benznidazole with a EC50 of 58.79 μM. Compounds 3, 4, 7, and 15 were the derivatives with the best selectivity index (SI) with values of 7.5, 8.3,12.1, and 8.6, respectively. Finally, compound 7 was the safer and the more promising derivative against T. cruzi.